Issue 6, 2023

Recent advances in 8π electrocyclization reactions

Abstract

Medium-ring systems, which constitute a class of structurally intriguing and biologically important molecules, are present in many natural products and pharmaceuticals. However, the construction of these skeletons tends to be difficult because of the torsional strain of the medium-sized ring, and control of the selectivity is also challenging in these flexible skeletons. Electrocyclization is one of the most straightforward methods to construct medium-sized rings and this process typically proceeds in a stereospecific manner, resulting in the stereo-controlled formation of two neighboring stereocenters. At present, there are few studies on 8π electrocyclization, mainly focusing on the synthesis of small molecules, while the applications in the synthesis of functional materials and biological contexts are rare. This feature article highlights recent advances, from 2000 to 2022, in the 8π electrocyclization reaction. This study is organized into four sections based on the size/composition of the target ring, including the synthesis of aza-seven-membered, cycloheptene, cyclooctene and bicyclo[4,2,0]octane frameworks. We expect that this feature article will provide beneficial guidance for the selective construction of medium-ring skeletons.

Graphical abstract: Recent advances in 8π electrocyclization reactions

Article information

Article type
Feature Article
Submitted
30 août 2022
Accepted
15 déc. 2022
First published
15 déc. 2022

Chem. Commun., 2023,59, 670-687

Recent advances in 8π electrocyclization reactions

L. Liu, L. Du and B. Li, Chem. Commun., 2023, 59, 670 DOI: 10.1039/D2CC04805A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements